MX2010005252A - Inhibidores de beta-lactamasa. - Google Patents
Inhibidores de beta-lactamasa.Info
- Publication number
- MX2010005252A MX2010005252A MX2010005252A MX2010005252A MX2010005252A MX 2010005252 A MX2010005252 A MX 2010005252A MX 2010005252 A MX2010005252 A MX 2010005252A MX 2010005252 A MX2010005252 A MX 2010005252A MX 2010005252 A MX2010005252 A MX 2010005252A
- Authority
- MX
- Mexico
- Prior art keywords
- group
- cycloalkyl
- aryl
- heteroaryl
- hydroxyl
- Prior art date
Links
- 239000003781 beta lactamase inhibitor Substances 0.000 title claims description 12
- 229940126813 beta-lactamase inhibitor Drugs 0.000 title claims description 12
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- -1 amino, carbonyl Chemical group 0.000 claims description 562
- 125000000623 heterocyclic group Chemical group 0.000 claims description 336
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 328
- 125000003118 aryl group Chemical group 0.000 claims description 319
- 125000001072 heteroaryl group Chemical group 0.000 claims description 315
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 302
- 229910052736 halogen Inorganic materials 0.000 claims description 286
- 150000002367 halogens Chemical group 0.000 claims description 286
- 125000001424 substituent group Chemical group 0.000 claims description 264
- 125000000217 alkyl group Chemical group 0.000 claims description 260
- 125000000304 alkynyl group Chemical group 0.000 claims description 254
- 125000003342 alkenyl group Chemical group 0.000 claims description 253
- 125000004104 aryloxy group Chemical group 0.000 claims description 251
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 251
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 251
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 248
- 125000003545 alkoxy group Chemical group 0.000 claims description 247
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 238
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 238
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 238
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 237
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 237
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 225
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 225
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 225
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 225
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 224
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 224
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 209
- 150000003573 thiols Chemical group 0.000 claims description 187
- 150000003462 sulfoxides Chemical class 0.000 claims description 159
- VXPNOKLAJJVEEG-UHFFFAOYSA-N 2-(diaminomethylideneamino)sulfanylguanidine Chemical compound NC(=N)NSNC(N)=N VXPNOKLAJJVEEG-UHFFFAOYSA-N 0.000 claims description 98
- 125000003375 sulfoxide group Chemical group 0.000 claims description 92
- 125000004432 carbon atom Chemical group C* 0.000 claims description 78
- 125000005842 heteroatom Chemical group 0.000 claims description 75
- 229910052757 nitrogen Inorganic materials 0.000 claims description 75
- 229910052760 oxygen Inorganic materials 0.000 claims description 75
- 239000001257 hydrogen Substances 0.000 claims description 74
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 150000002431 hydrogen Chemical class 0.000 claims description 53
- 125000004122 cyclic group Chemical group 0.000 claims description 51
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 35
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical group [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 31
- 229910052796 boron Inorganic materials 0.000 claims description 29
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims description 26
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000002132 β-lactam antibiotic Substances 0.000 claims description 26
- 229940124586 β-lactam antibiotics Drugs 0.000 claims description 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 22
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000004089 sulfido group Chemical group [S-]* 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000006467 substitution reaction Methods 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 14
- 229930186147 Cephalosporin Natural products 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 13
- 229940124587 cephalosporin Drugs 0.000 claims description 13
- 150000001780 cephalosporins Chemical class 0.000 claims description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 11
- 208000035143 Bacterial infection Diseases 0.000 claims description 10
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- 230000001580 bacterial effect Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 229930182555 Penicillin Natural products 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 206010034133 Pathogen resistance Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 4
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- LZKPUSJSJVEXAW-WDXSGGTDSA-N (4s,5r,6s)-3-[7-[1-(2-amino-2-oxoethyl)pyridin-1-ium-3-carbonyl]imidazo[5,1-b][1,3]thiazol-2-yl]-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C([O-])=O)=O)[C@H](O)C)C(SC1=2)=CN1C=NC=2C(=O)C1=CC=C[N+](CC(N)=O)=C1 LZKPUSJSJVEXAW-WDXSGGTDSA-N 0.000 claims description 2
- KLFSEZJCLYBFKQ-WXYNYTDUSA-N [(3s)-3-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1,5-dihydroxy-4-oxopyridin-2-yl)methoxyimino]acetyl]amino]-2,2-dimethyl-4-oxoazetidin-1-yl] hydrogen sulfate Chemical compound O=C1N(OS(O)(=O)=O)C(C)(C)[C@@H]1NC(=O)C(\C=1N=C(N)SC=1)=N/OCC1=CC(=O)C(O)=CN1O KLFSEZJCLYBFKQ-WXYNYTDUSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical compound OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims 4
- 206010041925 Staphylococcal infections Diseases 0.000 claims 4
- WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical compound O=C1N(S([O-])(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC([NH3+])=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-N 0.000 claims 4
- 229960003644 aztreonam Drugs 0.000 claims 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 claims 4
- 229960005090 cefpodoxime Drugs 0.000 claims 2
- WYUSVOMTXWRGEK-HBWVYFAYSA-N cefpodoxime Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC)C(O)=O)C(=O)C(=N/OC)\C1=CSC(N)=N1 WYUSVOMTXWRGEK-HBWVYFAYSA-N 0.000 claims 2
- 229960001991 ceftizoxime Drugs 0.000 claims 2
- NNULBSISHYWZJU-LLKWHZGFSA-N ceftizoxime Chemical compound N([C@@H]1C(N2C(=CCS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 NNULBSISHYWZJU-LLKWHZGFSA-N 0.000 claims 2
- 229940049954 penicillin Drugs 0.000 claims 2
- 235000019371 penicillin G benzathine Nutrition 0.000 claims 2
- 229950009297 pivoxil Drugs 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- JETQIUPBHQNHNZ-NJBDSQKTSA-N (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2r)-2-phenyl-2-sulfoacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H](C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)S(O)(=O)=O)=CC=CC=C1 JETQIUPBHQNHNZ-NJBDSQKTSA-N 0.000 claims 1
- XSPUSVIQHBDITA-KXDGEKGBSA-N (6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)/C(=N/OC)C=2N=C(N)SC=2)CC=1CN1N=NC(C)=N1 XSPUSVIQHBDITA-KXDGEKGBSA-N 0.000 claims 1
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 claims 1
- AMWKWIRXJXMMKB-UHFFFAOYSA-N 2-aminooxyguanidine Chemical compound NONC(N)=N AMWKWIRXJXMMKB-UHFFFAOYSA-N 0.000 claims 1
- HGGAKXAHAYOLDJ-FHZUQPTBSA-N 6alpha-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acid Chemical compound S([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1[C@H]1CCCO1 HGGAKXAHAYOLDJ-FHZUQPTBSA-N 0.000 claims 1
- WZPBZJONDBGPKJ-UHFFFAOYSA-N Antibiotic SQ 26917 Natural products O=C1N(S(O)(=O)=O)C(C)C1NC(=O)C(=NOC(C)(C)C(O)=O)C1=CSC(N)=N1 WZPBZJONDBGPKJ-UHFFFAOYSA-N 0.000 claims 1
- BHELIUBJHYAEDK-OAIUPTLZSA-N Aspoxicillin Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3[C@H](C(C)(C)S[C@@H]32)C(O)=O)=O)NC(=O)[C@H](N)CC(=O)NC)=CC=C(O)C=C1 BHELIUBJHYAEDK-OAIUPTLZSA-N 0.000 claims 1
- QYQDKDWGWDOFFU-IUODEOHRSA-N Cefotiam Chemical compound CN(C)CCN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC=3N=C(N)SC=3)[C@H]2SC1 QYQDKDWGWDOFFU-IUODEOHRSA-N 0.000 claims 1
- KEJCWVGMRLCZQQ-YJBYXUATSA-N Cefuroxime axetil Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(=O)OC(C)OC(C)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 KEJCWVGMRLCZQQ-YJBYXUATSA-N 0.000 claims 1
- JWCSIUVGFCSJCK-CAVRMKNVSA-N Disodium Moxalactam Chemical compound N([C@]1(OC)C(N2C(=C(CSC=3N(N=NN=3)C)CO[C@@H]21)C(O)=O)=O)C(=O)C(C(O)=O)C1=CC=C(O)C=C1 JWCSIUVGFCSJCK-CAVRMKNVSA-N 0.000 claims 1
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 claims 1
- JUZNIMUFDBIJCM-ANEDZVCMSA-N Invanz Chemical compound O=C([C@H]1NC[C@H](C1)SC=1[C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)NC1=CC=CC(C(O)=O)=C1 JUZNIMUFDBIJCM-ANEDZVCMSA-N 0.000 claims 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims 1
- TYMABNNERDVXID-DLYFRVTGSA-N Panipenem Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1S[C@H]1CCN(C(C)=N)C1 TYMABNNERDVXID-DLYFRVTGSA-N 0.000 claims 1
- 229930195708 Penicillin V Natural products 0.000 claims 1
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 claims 1
- 229960003022 amoxicillin Drugs 0.000 claims 1
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims 1
- 229960000723 ampicillin Drugs 0.000 claims 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims 1
- 229960000202 aspoxicillin Drugs 0.000 claims 1
- 229950003588 axetil Drugs 0.000 claims 1
- 229960003623 azlocillin Drugs 0.000 claims 1
- JTWOMNBEOCYFNV-NFFDBFGFSA-N azlocillin Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC=CC=1)C(=O)N1CCNC1=O JTWOMNBEOCYFNV-NFFDBFGFSA-N 0.000 claims 1
- 229960002699 bacampicillin Drugs 0.000 claims 1
- PFOLLRNADZZWEX-FFGRCDKISA-N bacampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)[C@H](C(S3)(C)C)C(=O)OC(C)OC(=O)OCC)=CC=CC=C1 PFOLLRNADZZWEX-FFGRCDKISA-N 0.000 claims 1
- MRMBZHPJVKCOMA-YJFSRANCSA-N biapenem Chemical compound C1N2C=NC=[N+]2CC1SC([C@@H]1C)=C(C([O-])=O)N2[C@H]1[C@@H]([C@H](O)C)C2=O MRMBZHPJVKCOMA-YJFSRANCSA-N 0.000 claims 1
- 229960003169 biapenem Drugs 0.000 claims 1
- 229960003669 carbenicillin Drugs 0.000 claims 1
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 claims 1
- UIMOJFJSJSIGLV-JNHMLNOCSA-N carumonam Chemical compound O=C1N(S(O)(=O)=O)[C@H](COC(=O)N)[C@@H]1NC(=O)C(=N/OCC(O)=O)\C1=CSC(N)=N1 UIMOJFJSJSIGLV-JNHMLNOCSA-N 0.000 claims 1
- 229960000662 carumonam Drugs 0.000 claims 1
- QYIYFLOTGYLRGG-GPCCPHFNSA-N cefaclor Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 QYIYFLOTGYLRGG-GPCCPHFNSA-N 0.000 claims 1
- 229960005361 cefaclor Drugs 0.000 claims 1
- 229960004841 cefadroxil Drugs 0.000 claims 1
- NBFNMSULHIODTC-CYJZLJNKSA-N cefadroxil monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=C(O)C=C1 NBFNMSULHIODTC-CYJZLJNKSA-N 0.000 claims 1
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 claims 1
- XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 claims 1
- 229960000603 cefalotin Drugs 0.000 claims 1
- OLVCFLKTBJRLHI-AXAPSJFSSA-N cefamandole Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](O)C=3C=CC=CC=3)[C@H]2SC1 OLVCFLKTBJRLHI-AXAPSJFSSA-N 0.000 claims 1
- 229960003012 cefamandole Drugs 0.000 claims 1
- 229960001139 cefazolin Drugs 0.000 claims 1
- MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 claims 1
- SMSRCGPDNDCXFR-CYWZMYCQSA-N cefbuperazone Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H]([C@H](C)O)C(=O)N[C@]1(OC)C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)C)CS[C@@H]21 SMSRCGPDNDCXFR-CYWZMYCQSA-N 0.000 claims 1
- 229960001817 cefbuperazone Drugs 0.000 claims 1
- HJJRIJDTIPFROI-NVKITGPLSA-N cefcapene Chemical group N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=C/CC)C1=CSC(N)=N1 HJJRIJDTIPFROI-NVKITGPLSA-N 0.000 claims 1
- JUVHVMCKLDZLGN-TVNFHGJBSA-N cefclidin Chemical compound N([C@@H]1C(N2C(=C(C[N+]34CCC(CC3)(CC4)C(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=NSC(N)=N1 JUVHVMCKLDZLGN-TVNFHGJBSA-N 0.000 claims 1
- 229950011467 cefclidin Drugs 0.000 claims 1
- 229960003719 cefdinir Drugs 0.000 claims 1
- RTXOFQZKPXMALH-GHXIOONMSA-N cefdinir Chemical compound S1C(N)=NC(C(=N\O)\C(=O)N[C@@H]2C(N3C(=C(C=C)CS[C@@H]32)C(O)=O)=O)=C1 RTXOFQZKPXMALH-GHXIOONMSA-N 0.000 claims 1
- 229960002142 cefditoren pivoxil Drugs 0.000 claims 1
- AFZFFLVORLEPPO-UVYJNCLZSA-N cefditoren pivoxil Chemical compound S([C@@H]1[C@@H](C(N1C=1C(=O)OCOC(=O)C(C)(C)C)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1\C=C/C=1SC=NC=1C AFZFFLVORLEPPO-UVYJNCLZSA-N 0.000 claims 1
- DASYMCLQENWCJG-XUKDPADISA-N cefetamet pivoxil Chemical compound N([C@@H]1C(N2C(=C(C)CS[C@@H]21)C(=O)OCOC(=O)C(C)(C)C)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 DASYMCLQENWCJG-XUKDPADISA-N 0.000 claims 1
- 229950000726 cefetamet pivoxil Drugs 0.000 claims 1
- 229960002129 cefixime Drugs 0.000 claims 1
- OKBVVJOGVLARMR-QSWIMTSFSA-N cefixime Chemical compound S1C(N)=NC(C(=N\OCC(O)=O)\C(=O)N[C@@H]2C(N3C(=C(C=C)CS[C@@H]32)C(O)=O)=O)=C1 OKBVVJOGVLARMR-QSWIMTSFSA-N 0.000 claims 1
- XAKKNLNAJBNLPC-MAYKBZFQSA-N cefluprenam Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)/C=C/C[N+](C)(CC)CC(N)=O)C([O-])=O)C(=O)C(=N/OCF)\C1=NSC(N)=N1 XAKKNLNAJBNLPC-MAYKBZFQSA-N 0.000 claims 1
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- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 229940041033 macrolides Drugs 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229960000282 metronidazole Drugs 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 229940041009 monobactams Drugs 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- XFGOMLIRJYURLQ-GOKYHWASSA-N razupenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)SC(SC=1)=NC=1C1=C[C@H](C)NC1 XFGOMLIRJYURLQ-GOKYHWASSA-N 0.000 description 1
- 230000008261 resistance mechanism Effects 0.000 description 1
- 229960001225 rifampicin Drugs 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 229960000268 spectinomycin Drugs 0.000 description 1
- UNFWWIHTNXNPBV-WXKVUWSESA-N spectinomycin Chemical compound O([C@@H]1[C@@H](NC)[C@@H](O)[C@H]([C@@H]([C@H]1O1)O)NC)[C@]2(O)[C@H]1O[C@H](C)CC2=O UNFWWIHTNXNPBV-WXKVUWSESA-N 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FKENQMMABCRJMK-RITPCOANSA-N sulbactam Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)C[C@H]21 FKENQMMABCRJMK-RITPCOANSA-N 0.000 description 1
- 229960005256 sulbactam Drugs 0.000 description 1
- 229960005404 sulfamethoxazole Drugs 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 1
- LPQZKKCYTLCDGQ-WEDXCCLWSA-N tazobactam Chemical compound C([C@]1(C)S([C@H]2N(C(C2)=O)[C@H]1C(O)=O)(=O)=O)N1C=CN=N1 LPQZKKCYTLCDGQ-WEDXCCLWSA-N 0.000 description 1
- 229960003865 tazobactam Drugs 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US279707P | 2007-11-13 | 2007-11-13 | |
| PCT/US2008/012705 WO2009064413A1 (fr) | 2007-11-13 | 2008-11-13 | Inhibiteurs de bêta-lactamases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2010005252A true MX2010005252A (es) | 2011-04-11 |
Family
ID=40344560
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2010005252A MX2010005252A (es) | 2007-11-13 | 2008-11-13 | Inhibidores de beta-lactamasa. |
| MX2010005250A MX2010005250A (es) | 2007-11-13 | 2008-11-13 | Inhibidores de beta-lactamasa. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2010005250A MX2010005250A (es) | 2007-11-13 | 2008-11-13 | Inhibidores de beta-lactamasa. |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US20100286092A1 (fr) |
| EP (2) | EP2220096A1 (fr) |
| JP (2) | JP2011503181A (fr) |
| KR (2) | KR20100109901A (fr) |
| CN (2) | CN101861324A (fr) |
| AR (2) | AR069310A1 (fr) |
| AU (2) | AU2008321443A1 (fr) |
| BR (2) | BRPI0820531A2 (fr) |
| CA (2) | CA2705389A1 (fr) |
| CO (1) | CO6331427A2 (fr) |
| CR (1) | CR11372A (fr) |
| EA (2) | EA201000774A1 (fr) |
| EC (1) | ECSP10010246A (fr) |
| GT (1) | GT201000143A (fr) |
| IL (1) | IL205205A0 (fr) |
| MA (1) | MA31874B1 (fr) |
| MX (2) | MX2010005252A (fr) |
| TN (1) | TN2010000203A1 (fr) |
| TW (2) | TW200930707A (fr) |
| WO (2) | WO2009064413A1 (fr) |
| ZA (1) | ZA201002467B (fr) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100120715A1 (en) * | 2007-11-13 | 2010-05-13 | Burns Christopher J | Beta-lactamase inhibitors |
| US20100292185A1 (en) * | 2009-05-12 | 2010-11-18 | Burns Christopher J | Beta-lactamase inhibitors |
| SG187757A1 (en) | 2010-08-10 | 2013-03-28 | Rempex Pharmaceuticals Inc | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| US9012491B2 (en) | 2011-08-31 | 2015-04-21 | Rempex Pharmaceuticals, Inc. | Heterocyclic boronic acid ester derivatives and therapeutic uses thereof |
| CA2860142C (fr) | 2011-12-22 | 2020-10-27 | Ares Trading S.A. | Derives d'acide alpha-amino boronique, inhibiteurs selectifs de l'immunoproteasome |
| MX2014008278A (es) | 2012-01-06 | 2014-11-10 | Univ South Florida | Composiciones, metodos de uso y metodos de tratamiento. |
| US8962843B2 (en) * | 2012-03-30 | 2015-02-24 | Cubist Pharmaceuticals, Inc. | 1,3,4-oxadiazole and 1,3,4-thiadiazole beta-lactamase inhibitors |
| US9156858B2 (en) | 2012-05-23 | 2015-10-13 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US10561675B2 (en) | 2012-06-06 | 2020-02-18 | Rempex Pharmaceuticals, Inc. | Cyclic boronic acid ester derivatives and therapeutic uses thereof |
| WO2014089365A1 (fr) | 2012-12-07 | 2014-06-12 | Venatorx Pharmaceuticals, Inc | Inhibiteurs de bêta-lactamase |
| CN104981239B (zh) * | 2013-01-04 | 2019-01-04 | 莱姆派克斯制药公司 | 硼酸衍生物及其治疗用途 |
| US9101638B2 (en) | 2013-01-04 | 2015-08-11 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| US9241947B2 (en) | 2013-01-04 | 2016-01-26 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| KR20150103269A (ko) * | 2013-01-04 | 2015-09-09 | 렘펙스 파머수티클스 인코퍼레이티드 | 보론산 유도체 및 그의 치료적 용도 |
| JP6346904B2 (ja) * | 2013-01-10 | 2018-06-20 | ベナトルクス ファーマシューティカルズ，インク． | ベータ−ラクタマーゼ阻害剤 |
| US9944658B2 (en) | 2013-03-14 | 2018-04-17 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| LT3140310T (lt) | 2014-05-05 | 2019-11-25 | Rempex Pharmaceuticals Inc | Boronato druskų sintezė ir jų panaudojimas |
| EP3139930A4 (fr) * | 2014-05-05 | 2018-01-17 | Rempex Pharmaceuticals, Inc. | Sels et polymorphes de dérivés cycliques d'ester d'acide boronique, et leurs utilisations thérapeutiques |
| EP3145936B1 (fr) * | 2014-05-19 | 2020-09-30 | Qpex Biopharma, Inc. | Dérivés d'acide boronique et leurs utilisations thérapeutiques |
| US9511142B2 (en) | 2014-06-11 | 2016-12-06 | VenatoRx Pharmaceuticals, Inc. | Beta-lactamase inhibitors |
| PT3154989T (pt) * | 2014-06-11 | 2021-05-18 | Venatorx Pharmaceuticals Inc | Inibidores de beta-lactamase |
| JP6700203B2 (ja) * | 2014-07-01 | 2020-05-27 | レンペックス・ファーマシューティカルズ・インコーポレイテッド | ボロン酸誘導体およびその治療的使用 |
| MX2017004043A (es) * | 2014-10-01 | 2017-07-04 | Merck Patent Gmbh | Derivados de acido boronico. |
| AU2015327346B2 (en) * | 2014-10-01 | 2019-12-05 | Merck Patent Gmbh | Boronic acid derivatives |
| RU2017115193A (ru) * | 2014-10-01 | 2018-11-06 | Мерк Патент Гмбх | Производные бороновой кислоты |
| WO2016081297A1 (fr) | 2014-11-18 | 2016-05-26 | Rempex Pharmaceuticals, Inc. | Dérivés d'esters d'acide boronique cycliques et leurs utilisations thérapeutiques |
| US10364257B2 (en) | 2014-12-19 | 2019-07-30 | Rempex Pharmaceuticals, Inc. | Apparatus and continuous flow process for production of boronic acid derivatives |
| US20180051041A1 (en) | 2015-03-17 | 2018-02-22 | Rempex Pharmaceuticals, Inc. | Boronic acid derivatives and therapeutic uses thereof |
| EP3347008B1 (fr) | 2015-09-11 | 2022-03-09 | Venatorx Pharmaceuticals, Inc. | Inhibiteurs de bêta-lactamases |
| WO2017100537A1 (fr) | 2015-12-10 | 2017-06-15 | VenatoRx Pharmaceuticals, Inc. | Inhibiteurs de bêta-lactamases |
| CN109563033B (zh) | 2016-06-21 | 2023-04-04 | 奥瑞恩眼科有限责任公司 | 脂族脯氨酰胺衍生物 |
| MY196909A (en) | 2016-06-30 | 2023-05-09 | Qpex Biopharma Inc | Boronic acid derivatives and therapeutic uses thereof |
| EP3494121B1 (fr) | 2016-08-04 | 2021-10-06 | Venatorx Pharmaceuticals, Inc. | Composés contenant du bore |
| BR112019018447A2 (pt) | 2017-03-06 | 2020-04-14 | Venatorx Pharmaceuticals Inc | formas sólidas e composições de combinação compreendendo um inibidor da beta-lactamase e usos das mesmas |
| EP3630782A4 (fr) * | 2017-05-26 | 2021-03-03 | Venatorx Pharmaceuticals, Inc. | Inhibiteurs de protéines de liaison à la pénicilline |
| US11267826B2 (en) | 2017-05-26 | 2022-03-08 | VenatoRx Pharmaceuticals, Inc. | Penicillin-binding protein inhibitors |
| WO2019009369A1 (fr) * | 2017-07-06 | 2019-01-10 | 大日本住友製薬株式会社 | Dérivé d'imine |
| TW201906616A (zh) * | 2017-07-06 | 2019-02-16 | 日商大日本住友製藥股份有限公司 | 醯胺衍生物 |
| EP3694864A4 (fr) | 2017-10-11 | 2021-10-13 | Qpex Biopharma, Inc. | Dérivés d'acide boronique et synthese de ces derniers |
| CN112424209A (zh) | 2018-04-20 | 2021-02-26 | Qpex生物制药有限公司 | 硼酸衍生物及其治疗用途 |
| MA54319A (fr) * | 2018-11-29 | 2021-10-06 | Venatorx Pharmaceuticals Inc | Compositions mixtes comprenant un inhibiteur de bêta-lactamase et leurs utilisations |
| CN110156820B (zh) * | 2019-04-25 | 2021-06-25 | 四川大学 | 一类巯基酰胺硼酸类衍生物及其作为mbl和/或sbl抑制剂的用途 |
| CN114340639A (zh) | 2019-06-19 | 2022-04-12 | Qpex生物制药有限公司 | 硼酸衍生物及其治疗用途 |
| CN113135944A (zh) * | 2020-01-19 | 2021-07-20 | 首药控股(北京)有限公司 | 硼酸衍生物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7112572B2 (en) * | 2002-09-09 | 2006-09-26 | Trigen Limited | Multivalent metal salts of boronic acids |
| US20060084592A1 (en) * | 2002-09-09 | 2006-04-20 | Trigen Limited | Peptide boronic acid inhibitors |
| US7271186B1 (en) * | 2002-12-09 | 2007-09-18 | Northwestern University | Nanomolar β-lactamase inhibitors |
| JP2007505950A (ja) * | 2003-06-10 | 2007-03-15 | フルクラム・ファーマシューティカルズ・インコーポレーテッド | β−ラクタマーゼ阻害剤およびその使用方法 |
| US20100120715A1 (en) * | 2007-11-13 | 2010-05-13 | Burns Christopher J | Beta-lactamase inhibitors |
| US20100292185A1 (en) * | 2009-05-12 | 2010-11-18 | Burns Christopher J | Beta-lactamase inhibitors |
-
2008
- 2008-11-13 AU AU2008321443A patent/AU2008321443A1/en not_active Abandoned
- 2008-11-13 JP JP2010534032A patent/JP2011503181A/ja not_active Withdrawn
- 2008-11-13 CN CN200880112051A patent/CN101861324A/zh active Pending
- 2008-11-13 EA EA201000774A patent/EA201000774A1/ru unknown
- 2008-11-13 US US12/742,526 patent/US20100286092A1/en not_active Abandoned
- 2008-11-13 AR ARP080104957A patent/AR069310A1/es unknown
- 2008-11-13 KR KR1020107012951A patent/KR20100109901A/ko not_active Application Discontinuation
- 2008-11-13 TW TW097143879A patent/TW200930707A/zh unknown
- 2008-11-13 EP EP08848632A patent/EP2220096A1/fr not_active Withdrawn
- 2008-11-13 BR BRPI0820531-0A patent/BRPI0820531A2/pt not_active Application Discontinuation
- 2008-11-13 WO PCT/US2008/012705 patent/WO2009064413A1/fr active Application Filing
- 2008-11-13 WO PCT/US2008/012706 patent/WO2009064414A1/fr active Application Filing
- 2008-11-13 MX MX2010005252A patent/MX2010005252A/es not_active Application Discontinuation
- 2008-11-13 AU AU2008321444A patent/AU2008321444A1/en not_active Withdrawn
- 2008-11-13 EA EA201000775A patent/EA201000775A1/ru unknown
- 2008-11-13 JP JP2010534031A patent/JP2011504468A/ja active Pending
- 2008-11-13 CA CA2705389A patent/CA2705389A1/fr not_active Abandoned
- 2008-11-13 CA CA2705393A patent/CA2705393A1/fr not_active Withdrawn
- 2008-11-13 TW TW097143877A patent/TW200936143A/zh unknown
- 2008-11-13 BR BRPI0820532-9A patent/BRPI0820532A2/pt not_active Application Discontinuation
- 2008-11-13 MX MX2010005250A patent/MX2010005250A/es not_active Application Discontinuation
- 2008-11-13 KR KR1020107012952A patent/KR20100113485A/ko not_active Application Discontinuation
- 2008-11-13 US US12/742,548 patent/US20100317621A1/en not_active Abandoned
- 2008-11-13 EP EP08848689A patent/EP2220097A1/fr not_active Withdrawn
- 2008-11-13 AR ARP080104956A patent/AR069463A1/es unknown
- 2008-11-13 CN CN2008801159624A patent/CN101983203A/zh active Pending
-
2010
- 2010-04-08 ZA ZA2010/02467A patent/ZA201002467B/en unknown
- 2010-04-15 CR CR11372A patent/CR11372A/es not_active Application Discontinuation
- 2010-04-19 IL IL205205A patent/IL205205A0/en unknown
- 2010-05-07 TN TN2010000203A patent/TN2010000203A1/fr unknown
- 2010-05-12 CO CO10056779A patent/CO6331427A2/es not_active Application Discontinuation
- 2010-05-13 GT GT201000143A patent/GT201000143A/es unknown
- 2010-05-31 MA MA32883A patent/MA31874B1/fr unknown
- 2010-06-11 EC EC2010010246A patent/ECSP10010246A/es unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |